With that additional qualification, it will get a bit more tricky. My first thought was to add a space to the character class: m,"?(/[^" ]*)"?,

But that doesn't work because it won't care that it has found a space inside or outside of a quote, and will stop the regex. Meaning it would capture just "/bootMe" from the line "/bootMe any text here".

I'd suggest looking into a module like Text::xSV or Text::CSV_XS and setting the delimiter to spaces. Then reject any entry that doesn't have a leading slash. This means dropping the regex entirely.

When putting a smiley right before a closing parenthesis, do you:

Use two parentheses: (Like this: :) )
Use one parenthesis: (Like this: :)
Reverse direction of the smiley: (Like this: (: )
Use angle/square brackets instead of parentheses
Use C-style commenting to set the smiley off from the closing parenthesis
Make the smiley a dunce: (:>
I disapprove of emoticons
Other